SYNTHETIC STUDIES ON THAXTOMIN-A AND THAXTOMIN-B, PHYTOTOXINS ASSOCIATED WITH STREPTOMYCES-SCABIES, THE CAUSAL ORGANISM OF POTATO COMMON SCAB

被引:23
作者
GELIN, J
MORTIER, J
MOYROUD, J
CHENE, A
机构
[1] RHONE POULENC SECTEUR AGRO,CTR RECH DARGOIRE,BP 9163,F-69263 LYON 09,FRANCE
[2] RHONE POULENC AG CO,RES TRIANGLE PK,NC 27709
关键词
D O I
10.1021/jo00065a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preliminary results of a study on the stereocontrolled racemic synthesis of thaxtomins A and B are disclosed. The synthesis features a new C-C bond-forming reaction: dilithium tetrachlorocuprate was shown to be an efficient catalyst for cross-coupling reactions of lithiated 1,4-dialkyl-2,5-piperazinedione anions with gramine methosulfate and alkyl halides.
引用
收藏
页码:3473 / 3475
页数:3
相关论文
共 31 条
[1]   CHIRAL ACYL ANION EQUIVALENTS - ASYMMETRIC SYNTHESIS OF ALPHA-METHOXYTOLUALDEHYDE [J].
COLOMBO, L ;
GENNARI, C ;
SCOLASTICO, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (13) :591-592
[2]   NEW TOTAL SYNTHESIS OF (+/-)-INDOLMYCIN [J].
DIRLAM, JP ;
CLARK, DA ;
HECKER, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4920-4924
[3]   SYNTHESIS AND STEREOCHEMISTRY OF INDOLACTAM-V, AN ACTIVE FRAGMENT OF TELEOCIDINS - STRUCTURAL REQUIREMENTS FOR TUMOR-PROMOTING ACTIVITY [J].
ENDO, Y ;
SHUDO, K ;
ITAI, A ;
HASEGAWA, M ;
SAKAI, S .
TETRAHEDRON, 1986, 42 (21) :5905-5924
[4]   IMPROVED CARBON-CARBON LINKING BY CONTROLLED COPPER CATALYSIS [J].
FOUQUET, G ;
SCHLOSSE.M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (01) :82-83
[5]   HALOPOLYCARBON HOMOLOGATION [J].
FRIEDMAN, L ;
SHANI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7101-7103
[6]   STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-QUINOCARCIN [J].
FUKUYAMA, T ;
NUNES, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) :5196-5198
[7]   TOTAL SYNTHESIS OF (+/-)-SAFRAMYCIN-A [J].
FUKUYAMA, T ;
YANG, L ;
AJECK, KL ;
SACHLEBEN, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3712-3713
[8]  
GALLINA C, 1973, TETRAHEDRON LETT, P1135
[9]   CONDENSATION OF 1,4-DIACETYLPIPERAZINE-2,5-DIONE WITH ALDEHYDES [J].
GALLINA, C ;
LIBERATORI, A .
TETRAHEDRON, 1974, 30 (05) :667-673
[10]   SYNTHESIS OF 1,3,4,5-TETRAHYDROPYRROLO(4,3,2-DE)QUINOLINE [J].
HESTER, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) :1158-&